Thiophene or furan herbicides

ABSTRACT

Novel thiophenes or furans show herbicidal activity and may also have post- and pre-emergence crop tolerance, especially to corn.

RELATED APPLICATION

This application is a continuation-in-part of my copending applicationU.S. Ser. No. 247,134, filed Mar. 24, 1981, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel thiophene or furan herbicides and theiruse as agricultural chemicals. In particular, they are useful as pre-and post-emergence herbicides and as plant growth regulants. Certaincompounds within the scope of the instant invention have shown cropselectivity and in particular have shown selectivity toward corn.

Levitt U.S. Pat. No. 4,169,719 discloses herbicidal thiophene and furansulfonylureas such as: ##STR1## wherein

R₈ is H, Cl, Br or CH₃ ;

R₉ is H, Cl, Br or CH₃ ;

R₁₀ is H, Cl, Br or CH₃ ;

X is H, Cl, Br, CH₃, C₂ H₅, C₁ -C₃ alkoxy, CF₃, SCH₃ or CH₂ OCH₃ ;

Z is CH₃ or OCH₃ ; and

Q is sulfur or oxygen.

Levitt U.S. Pat. No. 4,127,405 discloses herbicidal thiophene and furansulfonylureas such as, ##STR2## wherein R₈, R₉, R₁₀, Q, X and Z aredefined as above.

U.S. Ser. No. 153,279 now abandoned discloses herbicidal thiophenesulfonylureas such as, ##STR3## wherein

A is ##STR4##

R is C₁ -C₄ alkyl, NO₂, Cl, Br or SO₂ NR₁ R₂ ; and

R₁ and R₂ are independently C₁ -C₃ alkyl.

U.S. Ser. No. 196,267 now abandoned discloses herbicidal thiophenesulfonylureas such as, ##STR5## wherein

A¹ is H, Cl, Br, C₁ -C₄ alkyl, OCH₃, NO₂ or CF₃ ;

A is ##STR6## and;

B is ##STR7##

R₄ is H or CH₃ ;

R₅ is H, CH₃ or OCH₃ ; and

R₁ is ##STR8##

J. Drug. Res. 6, 123 (1974) discloses antidiabetic thiophenesulfonylthioureas such as, ##STR9## where R is pyridyl.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodneeds, such as soybeans, barley, wheat, and the like. The currentpopulation explosion and concomitant world food shortage demandimprovements in the efficiency of producing these crops. Prevention orminimizing the loss of a portion of valuable crops by killing, orinhibiting the growth of undesired vegetation is one way of improvingthis efficiency.

A wide variety of materials useful for killing, or inhibiting(controlling) the growth of undesired vegetation is available; suchmaterials are commonly referred to as herbicides. The need exists,however, for still more effective herbicides that destroy or retardweeds without causing significant damage to useful crops.

SUMMARY OF THE INVENTION

This invention relates to compounds of Formula I and theiragriculturally suitable salts, suitable agricultural compositionscontaining them, and method of using them as pre-emergence and/orpost-emergence herbicides. ##STR10## wherein Q is 0 or S;

A is ##STR11## R₁ is R₆ S[O]_(n) ;

R₆ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, cyclopentyl or cyclopropylmethyl;

R₂ is H, Cl, Br or CH₃ ;

R₃ and R₄ are independently H or CH₃ ; n is 0, 1 or 2; and

R₅ is ##STR12## wherein

X is CH₃ or OCH₃ ;

Y is H, Cl, CH₃, C₂ H₅, OCH₃, OC₂ H₅ or CH₂ OCH₃ ;

Y₁ is H, Cl, CH₃ or OCH₃ ;

Y₂ is CH₃ or OCH₃ ;

Z is CH or N;

and their agriculturally suitable salts; provided that:

both R₃ and R₄ may not simultaneously be CH₃, and further provided thatR₁ and A are bonded to adjacent carbon atoms of the thiophene or furanring.

PREFERRED COMPOUNDS

Preferred for their higher herbicidal activity and/or more favorableease of synthesis are:

(1) Compounds of Formula I where Q is S;

(2) Compounds of Preferred (1) where R₂ is H;

(3) Compounds of Preferred (2) where R₆ is C₁ -C₃ alkyl;

(4) Compounds of Preferred (3) where n is 2;

(5) Compounds of Preferred (4) where R₅ is ##STR13##

(6) Compounds of Preferred (5) where R₃ is H;

(7) Compounds of Preferred (6) with the structure ##STR14##

(8) Compounds of Preferred (6) with the structure ##STR15##

(9) Compounds of Preferred (6) with the structure ##STR16##

(10) Compounds of Preferred (7) where X is CH₃ or OCH₃ ; and Y is CH₃,OCH₃, OC₂ H₅ or CH₂ OCH₃ ;

(11) Compounds of Preferred (8) where X is CH₃ or OCH₃ ; and Y is CH₃,OCH₃, OC₂ H₅ or CH₂ OCH₃ ;

(12) Compounds of Preferred (9) where X is CH₃ or OCH₃ ; and Y is CH₃,OCH₃, OC₂ H₅ or CH₂ OCH₃ ;

(13) Compounds of Preferred (10) where R₄ is H;

(14) Compounds of Preferred (11) where R₄ is H;

(15) Compounds of Preferred (12) where R₄ is H;

(16) Compounds of Formula I where Q is O;

(17) Compounds of Preferred (16) where R₂ is H;

(18) Compounds of Preferred (17) where R₆ is C₁ -C₃ alkyl;

(19) Compounds of Preferred (18) where n is 2;

(20) Compounds of Preferred (19) where R₅ is ##STR17##

(21) Compounds of Preferred (20) where R₃ is H;

(22) Compounds of Preferred (21) with the structure ##STR18##

(23) Compounds of Preferred (21) with the structure ##STR19## and

(24) Compounds of Preferred (21) with the structure ##STR20##

Specifically Preferred compounds for highest herbicidal activity and/ormost favorable ease of synthesis are:

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;

N-[(4,6-dimetoxypyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;

N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;

N-[(4,6-dimethoxypyrimidin-2-yl)(methyl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;

N-[(4-methoxy-6-methylpyrimidin-2-yl)(methyl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)(methyl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide;and

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)(methyl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide.

The invention also relates to compounds of Formula II which are usefulas intermediates for the preparation of compounds of Formula I.##STR21## wherein

Q is O or S;

R₁ is R₆ S[O]_(n) ;

R₆ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, cyclopentyl or cyclopropylmethyl;and

n is 0 or 2;

provided that:

R₁ and the sulfonylisocyanate group are bonded to adjacent carbon atomsof the furan or thiophene ring.

PREFERRED INTERMEDIATES

Preferred intermediates for the higher herbicidal activity of productsderived from them and/or their more favorable ease of synthesis are:

(1) Compounds of Formula II with the structure ##STR22##

(2) Compounds of Formula II with the structure ##STR23##

(3) Compounds of Formula II with the structure ##STR24## and

(4) Compounds of Preferred (2) wherein R₁ is R₆ SO₂, and R₆ is C₁ -C₃alkyl.

The invention also relates to compounds of Formula III which are usefulas intermediates for the preparation of compounds of Formula I.##STR25## wherein

Q is O or S;

R₁ is R₆ S[O]_(n) ;

R₆ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, cyclopentyl or cyclopropylmethyl;

n is 0 or 2; and

Z is CH or N.

provided that:

R₁ and the sulfonylureido group are bonded to adjacent carbon atoms ofthe furan or thiophene ring.

SYNTHESIS

Many of the compounds of Formula IA, IB and IC, wherein n=0 or 2, R₃ =Hand Q, R₂, and R₆ are as previously defined, may be prepared as shown inEquation 1 by the reaction of the appropriately substituted furan orthiophenesulfonylisocyanates, II, wherein n=0 or 2 and Q, R₂ and R₆ areas previously defined, with the appropriate heterocyclic amine, V,wherein R₄ and R₅ are as previously defined. ##STR26##

The reactions of Equation 1 are generally carried out by contacting asolution of the isocyanates of Formula II in an inert solvent such asmethylene chloride or acetonitrile with the appropriate heterocyclicamine V and isolating the product either by filtration or by evaporationof solvent and trituration or column chromatography.

From the compounds of Formula VI, wherein A, Q, R₂ and R₆ are aspreviously defined, the compounds of Formula VIII may be prepared byoxidation, as shown in Equation 2. ##STR27##

The oxidation of Equation 2 is carried out by mixing equimolarquantities of the appropriate sulfide (VI) and m-chloroperbenzoic acid(VII) in an inert solvent such as methylene chloride at 0°-25° andisolating the product by column chromatography or filtration.

The compounds of Formula IX, wherein R₆ =C₁ -C₄ alkyl, cyclopentyl andcyclopropylmethyl, and Q, R₂ and A are as previously defined, may beprepared by oxidation as in Equation 2, but using twice the equivalentamount of oxidant (VII) and heating the solution at 40°-70° for 1-7days. ##STR28##

Alternatively, oxidation of sulfides of Formula VI to sulfoxides ofFormula VIII or sulfones of Formula IX can be carried out employingaqueous hydrogen peroxide in acetic acid by methods well known in theart.

Compounds of Formula I can also be prepared by the method described inEquation 4. ##STR29## wherein Q, R₁, R₂, R₃ and Z are as previouslydefined, and R₇ is CH₃ or C₂ H₅.

Reaction Step (4a)

In Reaction Step (4a), a furan or thiophenesulfonamide of Formula X iscontacted with a heterocyclic isocyanate of Formula XI to yield asulfonylurea of Formula III.

The heterocyclic isocyanates used in Reaction (4a) may be preparedaccording to methods described in Swiss Pat. No. 579,062, U.S. Pat. No.3,919,228, U.S. Pat. No. 3,732,223 and Angew Chem. Int. Ed. 10, 402(1976), the disclosures of which are herein incorporated by reference.

The furan or thiophene sulfonamide and the heterocyclic isocyanate arecontacted in the presence of an inert organic solvent, for example,acetonitrile, tetrahydrofuran (THF), toluene, acetone or butanone.Optionally, a catalytic amount of a base, such as1,4-diazabicyclo[2.2.2]octane (DABCO), potassium carbonate, sodiumhydride or potassium tert-butoxide, may be added to the reactionmixture. The quantity of base constituting a catalytic amount would beobvious to one skilled in the art. The reaction mixture is preferablymaintained at a temperature of about 25° to 110° C., and the product cangenerally be recovered by cooling and filtering the reaction mixture.For reasons of efficiency and economy, the preferred solvents areacetonitrile and THF, and the preferred temperature range is about 60°to 85° C.

Reaction Steps (4b) and (4c)

In Reaction Steps (4b) and (4c), one or two of the chlorine atoms on thepyrimidinyl or triazinyl ring of the compound of Formula III isdisplaced by an alcohol. Generally, this may be done by contacting thecompound of Formula III with methanol or methoxide. Thus, in ReactionStep 4b, a compound of Formula III may be contacted with at least oneequivalent of methanol. This reaction is sluggish, however, and it ispreferred to contact the compound of Formula III with at least twoequivalents of sodium methoxide in either methanol, acetonitrile, THF ordimethylformamide.

It should be noted that two equivalents of methoxide are required forReaction Step (4b) whereas only one equivalent of methanol is needed forthe same process. This difference is due to the reaction which isbelieved to occur between the methoxide and the sulfonyl nitrogen of thesulfonamide of Formula III. When methoxide is used, the first equivalentof base removes a proton from the sulfonyl nitrogen, and it is only thesecond equivalent which effects displacement of the halogen. As aresult, two equivalents of methoxide are required. The resulting saltmust be acidified, e.g., with sulfuric, hydrochloric or acetic acid, toyield a compound of Formula XIII. Applicant, of course, does not intendto be bound by the mechanism described above.

In Reaction Step (4c) a compound of Formula XIII, is contacted witheither one equivalent of alkanol, R₇ OH, or with two equivalents ofalkoxide, R₇ O⁻ where R₇ is as described above.

When R₇ =CH₃, Reaction Steps (4b) and (4c) may be combined. Thus, acompound of Formula III may be contacted either with at least twoequivalents of methanol, or with at least three equivalents ofmethoxide. In Reaction Step 4b, certain reaction conditions will favordisplacement of only one chlorine atom. These conditions are the use oflow temperatures and the slow addition of the stoichiometric amount ofalkoxide or alkoxide-generating base to the medium containing thecompound of Formula III.

Both Reaction Steps (4b) and (4c) are preferably run at temperatureswithin the range of about -10° to 80° C., the range of about 0° to 25°C. being more preferred. Reaction Steps (4b) and (4c) are more sluggishwhen alkanol is used instead of alkoxide, and more drastic conditionsare required for the reaction to go to completion. Thus, highertemperatures, up to and including the boiling point of the alkanolitself, are required.

The novel furan or thiophenesulfonyl isocyanates of Formula II, whereinn=0 or 2 and Q and R₁ are as previously defined, are importantintermediates in the preparation of the compounds of this invention. Themethod by which they can be prepared from sulfonamides of Formula XV,wherein n=0 or 2 and Q, R₆ and R₂ are as previously defined, is shown inEquation 5, by methods taught in G. Levitt, U.S. Pat. No. 4,169,719, thedisclosures of which are herein incorporated by reference. ##STR30##

The preparation of the novel sulfonamides of Formulae XXIV or XXV may beaccomplished by the method outlined in Equation 6. ##STR31## wherein R₂and R₆ are as previously defined, and R₈ =n-Bu, --N(i-C₃ H₇)₂, t-Bu, or##STR32##

The sulfonyl chlorides of Formula XVII are described by H. D. Hartoughin "The Chemistry of Heterocyclic Compounds," v. 3, IntersciencePublishers, Inc., N.Y. 1952. These may be converted to the correspondingN-t-butyl sulfonamides (XVIII) by admixture with at least twice theequivalent amount of t-butylamine in an inert solvent, such as ether,filtration of the amine hydrochloride, and evaporation of solvent. Thelithiation of thiophenes and of aromatic N-t-butylsulfonamides withn-butyllithium, t-butyllithium, lithium diisopropylamide and lithium2,2,6,6-tetramethyl piperidide is reviewed by H. W. Gschwend and H. R.Rodriguez in Org. React., 26, 1 (1979), and is generally carried out bycooling to -78° a solution of twice the equimolar amount of XIX, keptunder an inert atmosphere, in an ethereal solvent such as diethyl etheror THF, and adding a solution of the compound of Formula XVIII. Thecompounds of Formula XXI may be prepared as shown in Equation (6b) byadding an equimolar quantity of the appropriate disulfide (XX), allowingthe mixture to warm to room temperature, washing the mixture with acidicbrine, and evaporation of the solvent.

Alternatively, as shown in Equation (6c), in order to prepare thecompounds of Formula XXIII, the lithiation mixture may be treated withan equimolar quantity of sulfur dioxide, allowing the mixture to warm toroom temperature, filtration of the solid precipitate, dissolution ofthis salt in ethanol and adding an equimolar amount of the appropriatealkyl iodide (XXII). This alkylation step may be carried out attemperatures of 25° to 78°. The cooled reaction mixture may be dilutedwith dilute aqueous hydrochloric acid to precipitate the product(XXIII). The t-butyl sulfonamides of Formula XXI and XXIII may beconverted to the compounds of Formulae XXIV and XXV, respectively, byheating in methanol containing at least an equimolar quantity ofhydrochloric acid, followed by concentration of the reaction mixture andprecipitation of the product with ether. Compounds of Formula XXV may beprepared by the reaction of Equation (6f), which is carried out asdescribed for Equation 3.

An alternate preparation of the thiophene sulfonamides of Formula XXV isdescribed in Equation 7. ##STR33## wherein

R₆ =C₁ -C₄ alkyl, cyclopentyl, cyclopropylmethyl;

R₉ =Cl, Br; and

R₂ =H, CH₃, Cl and 4-Br.

The reaction of Equation (7a) is accomplished by mixing equimolarquantities of the appropriate halide (XXVI) with an equimolar quantityof benzyl mercaptan in a polar solvent, such as dimethylformamide,containing an equimolar amount of a strong base, such as sodiummethoxide or sodium hydride, heating at a temperature between 50° and120°, and isolating the product by precipitation with ice-water andwashing with hexane. The sulfides of Formula XXVII are converted to thesulfonyl chlorides (XXVIII) as shown in Equation (7b) by contacting withat least three equivalents of chlorine in acetic acid according to theprocedure of R. F. Langler, Can. J. Chem., 54, 498 (1976). The sulfonylchlorides can be precipitated by the addition of ice-water to thechlorination mixture. Ammonolysis of thiophene sulfonyl chlorides(XXVIII) is described by Hartough, loc. cit. The sulfone (XXVI), whereinR₂ =H, R₆ =CH₃ and R₉ =Br, is described by D. Spinelli, et al., J. Chem.Soc. Perkin II, 1972, 441. The preparation of analogous compounds ofFormula XXVI will be obvious to one skilled in the art.

The compounds of Formulae XXXI and XXXII, wherein R₂ is as previouslydefined, may be prepared according to the method outlined in Equation 8.##STR34##

The compounds of Formula XXX, wherein R is as previously defined and R₆is C₁ -C₄ alkyl or cyclopentyl, may be prepared by adding twice theequimolar amount of chlorosulfonic acid, diluted in an inert solvent,such as dichloromethane, to the appropriate 3-thienyl alkyl sulfide(XXIX) at temperatures between -30° and 25°, washing the mixture withice-water and evaporating the solvent. These may be converted to theappropriate compounds of Formula XXXI by contacting with ammonia. Thesulfides of Formula XXXI may be oxidized exactly as described inEquation 2 to compounds of Formula XXXII.

Alternatively, the methods described in Equation 6 may be applied to thecompounds of Formula XXXIII to produce compounds of Formulae XXXI andXXXII as shown in Equation 9. ##STR35## wherein R₂, R₆ and R₈ are aspreviously defined.

The preparation of the compounds of Formulae XLII and XLIV can beaccomplished according to the method outlined in Equation 10. ##STR36##wherein

R₁₀ =Cl or CH₃ ;

R₁₁ =Cl, Br or CH₃, provided that R₁₀ and R₁₁ cannot both be CH₃ ;

R₂ =H, Cl, Br or CH₃ ; and

R₆ and R₈ are as previously defined.

Starting with sulfonyl chlorides of Formula XXXVII (Hartough, loc.cit.), the procedure described above can be used, analogously toEquation 6, to prepare the compounds of Formulae XXXIX and XL. Thesedihalo-compounds may be partially dehalogenated by contacting with twoequivalents of 5% sodium amalgam in an alcoholic or aqueous alcoholicsolution at 25° to 78°, followed by acidification with aqueoushydrochloric acid at 0° and filtration or extraction of the products ofFormulae XLI or XLIII wherein R₂ =Cl or Br. The 2-halo and 5-haloisomers may be separated by column chromatography. The totallydehalogenated compounds of Formulae XLI or XLIII wherein R₂ =H may beprepared by using three or more equivalents of the sodium amalgam in thereaction. These compounds may be converted to the compounds of FormulaeXLII or XLIV as previously described.

The furan sulfonamides of Formula XV may be prepared from halofurans orhalofuran carboxylic acids, which are described by A. P. Dunlop and F.N. Peters in "The Furans," Reinhold, New York, 1953.

The sulfonamides of Formula XLII or XLIX may be obtained by thereactions of Equation 11. ##STR37## wherein

X=Br or I;

M=Na, K or Cu; and

R₂ and R₆ are as previously defined.

The reaction of Equation 11a is carried out by contacting a compound ofFormula XLV with an alkali metal or copper (I) salt of the appropriatealkyl thiol in a polar, aprotic solvent (such as dimethylformamide orN-methylpyrrolidone) at 50° to 150° C., followed by extraction orfiltration from dilute aqueous acid. The compounds of Formula XLVIwherein R₁₂ is CH₃ or C₂ H₅ may be saponified and acidified to affordthe compounds of Formula XLVI wherein R₁₂ is H. These may bedecarboxylated by heating in a solvent such as quinoline in the presenceof copper powder or copper bronze. The reactions of Equation 11c and 11dmay be carried out as described for Equations 8a, 8b and 8c.

The sulfonamides of Formula LIII and LIV may be prepared from sulfonylchlorides of Formula LII in a manner exactly analogous to that describedfor Equations 6b-6e. ##STR38## wherein

X is Br or I;

R₂ and R₆ are as previously defined.

The preparation of the sulfonyl chlorides LII is shown in Equations 12aand 12b, wherein an ethereal solution of the appropriate bromo- oriodofuran L is treated with one equivalent of butyllithium at -78° to-100° C., one equivalent of sulfur dioxide is added, and the salt LI isfiltered. The reaction of Equation 12b is carried out by cooling asuspension or solution of LI in an inert solvent such as acetone to -20°to 0° C., adding one equivalent of a weak acid, such as acetic acid,followed by one equivalent of a chlorinating agent, such asN-chlorosuccinimide. The product is isolated by evaporation of thesolvent, and washing an ether solution of the residue with water toremove the by-products of the reaction. This solution of LII may be usedin the sequence described for equations 6b and 6d or 6C and 6e toproduce compounds of Formula LIII or LIV, respectively.

The sulfonamides of Formulas LIX or LX may be prepared according to thereactions of Equation 13. ##STR39## wherein

R₂ is CH₃, Cl or Br; and

R₆ and R₈ are as previously defined.

The appropriately substituted furansulfonyl chlorides LV may be preparedby methods described by A. P. Dunlop and F. N. Peters, loc. cit., andaminated by t-butylamine, saponified, and acidified to afford thecompounds of Formula LVI. The reaction of Equation 13 is carried out bytreatment of a solution of a compound of Formula LVI in tetrahydrofuranwith three equivalents of base XIX such as butyllithium at -78° to 0° C.followed by treatment of the resulting furanyllithium solution with theappropriate disulfide analogously to Equation 10b. The compounds ofFormula LVII may be solvolyzed and decarboxylated as describedpreviously to afford the compounds of Formula LIX. Analogously toEquations 10c and 10e, the compounds of Formula LX may be prepared fromLVI.

The compounds of Formula LXVI and LXVII may be prepared by the reactionsof Equation 14. ##STR40## wherein

R₁₂ is CH₃ or C₂ H₅ ;

R₂ is CH₃, Cl or Br; and

R₆ and R₈ are as previously defined.

The reaction of Equations 14a and 14b are carried out as described forEquations 7a and 7b, and the reactions of Equations 14c, 14d, 14e, 14f,and 14g are carried out as described for Equations 13a, 13b, 13c, 13d,and 13e, respectively.

Finally, the compounds of Formula LXVIII or LXIX may be preparedaccording to the method of Equation 15, which is carried out asdescribed for Equation 10d. ##STR41##

The synthesis of heterocyclic amines of Formula V has been reviewed in"The Chemistry of Heterocyclic Compounds," a series published byInterscience Publishers, Inc., N.Y. and London. 2-Aminopyrimidines aredescribed by D. J. Brown in The Pyrimidines, Vol. 26 of this series. The2-amino-1,3,5-triazines are reviewed by K. R. Huffman in "the Triazines"of this same series. The synthesis of triazines is also described by F.C. Schaefer, U.S. Pat. No. 3,154,547, and by K. R. Huffman and F. C.Schaefer, J. Org. Chem., 28, 1816 (1963). The 4-aminopyrimidines aredisclosed in U.S. Pat. No. 4,221,585, and the 2-amino-1,3,4-triazinesare disclosed in U.S. Pat. No. 4,120,691. The synthesis of the bicyclicheterocyclic amines LXX and LXXI wherein Y₁ is as previously defined areprepared as described in the unexamined European Patent No. 15-683,published Sept. 17, 1980. ##STR42##

The pyrimidine intermediate (LXXIX) in which Y₁ is methyl have beenreported in the literature by E. Bisagni et al., [Bull. Soc. Chim. Fr.,803 (1969)]. An apparently more efficient procedure is depicted inEquation 16. ##STR43##

The keto-ester precursors (LXXII) are prepared by well known literaturemethods, e.g., J. F. Tinker and T. E. Whatmough, J. Amer. Chem. Soc., 745235 (1952).

Treatment of (LXXII) with an excess of guanidine carbonate in an organicsolvent, preferably a polar aprotic solvent such as dimethylsulfoxide(DMSO), dimethylformamide (DMF), or N,N-dimethylacetamide, at atemperature of 80° to 200°, preferably 100° to 160°, ambient pressureand preferably under an inert atmosphere, yields both (LXXIX) and(LXXIII) as products. The products are isolated upon dilution of thereaction mixture with, for example, acetone and water successively.Higher reaction temperatures and longer reaction times (e.g., in DMSO at130°-150° for 2 to 8 hours) favor the production of the furopyrimidine(LXXIX) over the uncyclized pyrimidine (LXXIII).

The pyrimidine intermediate (LXXXIII) in which Y₁ is a chlorine atom maybe prepared by condensing the known ethyl 2-carbethoxy-4-pentynoate(LXXX) with guanidine carbonate in an alcohol solvent such as ethanol togive the intermediate pyrimidine (LXXXI) as shown in Equation 17.##STR44##

Conversion to the dichloropyrimidine (LXXXII) may be accomplished byheating (LXXXI) in phosphorus oxychloride. The product (LXXXII) may beisolated by removal of the phosphorus oxychloride at reduced pressure,trituration of the residue with ice-water and filtration of the solidproduct. Reaction of this dichloropyrimidine (LXXXII) with twoequivalents of an aqueous alkali metal hydroxide, such as sodiumhydroxide, yields the cyclized furopyrimidine (LXXXIII) as a majorproduct. The reaction is best carried out in the presence of asolubilizing organic solvent that is water miscible, such astert-butanol, dioxane or tetrahydrofuran, and at temperatures from 20°to 100° or conveniently at the boiling point of the solvent mixtureused. The product may be isolated by cooling the mixture and furtherdilution with water to effect precipitation.

Compounds of Formula LXXXIV which are also used as intermediates for thesulfonylurea herbicides of this invention may be prepared from thechlorofuropyrimidine. (LXXXIII) by reaction with sodium methoxide inboiling methanol, as shown in Equation 18. The product is obtained uponevaporation of the methanol solution and trituration of the residue withcold water and subsequent filtration. ##STR45##

The intermediates of Formula LXXXV in which Y₁ is hydrogen may beprepared by reduction of the chlorofuropyrimidine (LXXXIII) with areducing agent such as zinc dust in acetic acid or p-toluenesulfonylhydrazide; the latter by a procedure similar to that described by Albertand Royer, J. Chem. Soc., 1148 (1949). ##STR46##

Many of the aminoheterocyclic intermediates of Formula V where R₄ ismethyl or methoxy may be prepared by the following two-step procedure asshown in Equation 20. ##STR47## wherein X, Y and Z are as previouslydefined and R₄ is methyl or methoxy.

A solution of the amine (LXXXVI) in concentrated hydrochloric acid istreated with sodium nitrite solution and the chloro compound (LXXXVII)is isolated in the usual manner by filtration of the acidic solution. Arepresentative procedure is described by Bee and Rose in J. Chem. Soc.C, 2031 (1966), for the case in which Z=CH, and X=Y=OCH₃. Displacementof the chlorine of (LXXXVII) may be accomplished by heating with anexcess of methylamine or O-methyl hydroxylamine in water to obtain themethylamino heterocycle (LXXXVIII) or N-methoxyamino heterocycle(LXXXVIII).

The synthesis of the bicyclic amines of Formula LXXXIX is disclosed inEur. Pat. No. 803 005 05.7.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by treating compounds of Formula I witha solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g. hydroxide, alkoxide, carbonate orhydride) quaternary amine salts can be made by similar techniques.Detailed examples of such techniques are given in U.S. Pat. No.4,127,405, the disclosure of which is herein incorporated by reference.

In the following examples, unless otherwise indicated, all parts are byweight and temperatures in °C.

EXAMPLE 1 3-Benzylthio-2-thienyl methyl sulfone (XXVII)

To a solution of 2 g of sodium methoxide in 100 ml of dimethylformamidewas added 6 ml of benzyl mercaptan followed by 10 g of 3-bromo-2-thienylmethyl sulfone. The temperature rose to 70°. The mixture was stirred atroom temperature for 16 hours and then at 70° for 1 hour. Most of thedimethylformamide was evaporated at reduced pressure and ice-water wasadded to the residue. The resulting solid was filtered, washed withice-water and hexane to afford 14 g of crude XXVII. A dried sample ofthis material had m.p. 95°-97° and peak at 4.2 in the NMR spectrum(CDCl₃), consistent with an aromatic benzyl sulfide.

EXAMPLE 2 2-Methylsulfonyl-3-thiophenesulfonyl chloride (XXVIII)

To 14 g of (XXVII) in 200 ml of acetic acid was added chlorine gas at15°-20° until a green color persisted. The mixture was stirred for 1hour at 15°-20° and then purged with nitrogen, poured into ice-water,and then with hexane to afford 13 g of crude (XVIII). A dried sample hadm.p. 116°-120° and an NMR spectrum (CDCl₃) which showed peaks at δ3.4(CH₃ SO₂ --) and δ7.8 (AB, J=5 Hz), consistent with a thienyl methylsulfone.

EXAMPLE 3 2-Methylsulfonyl-3-thiophenesulfonamide (XXV)

To 10 g of (XXVIII) in 200 ml of ethyl acetate was added 5 ml of liquidammonia with stirring at 0°. The mixture was allowed to attain roomtemperature, evaporated and the solid product was washed with ice-water.A dried sample of (XXV) had m.p. 242°-244°.

EXAMPLE 4 N-(Butylaminocarbonyl)-2-methylsulfonyl-3-thiophenesulfonamide

A solution of 4.0 g of (XXV) and 2.0 ml of n-butyl isocyanate in 50 mlof 2-butanone was heated at reflux with 2.0 g of anhydrous potassiumcarbonate for 7 hours. The cooled mixture was filtered, the solids werewashed with ice-water, and the combined filtrate and washings wereacidified with 2 N HCl. The precipitate was filtered and washed withwater to afford 2.4 g of the n-butylaminocarbonyl derivative of (XXV),m.p. 173.5°-174°. The NMR spectrum (CDCl₃ /DMSO-d₆) exhibited peaks atδ0.7-1.7 (m, 7H), 2.8-3.3 (m, 2H) and 6.4 (t, 1H) indicative of anN-butylurea.

EXAMPLE 5 2-Methylsulfonyl-3-thiophenesulfonyl isocyanate

A suspension of 3.3 g of the (N-(n-butylamino carbonyl) derivative of(XXV) in 75 ml of xylene containing 0.5 g of DABCO was heated to125°-130° and a solution of 1.8 ml of liquid phosgene in 2 ml of xylenewas added. The mixture was heated at reflux for an additional 1.5 hour,cooled under nitrogen, and concentrated to dryness in vacuo. A sample ofthe crude product displayed a characteristic sulfonyl isocyanate band inthe IR at 2200 cm⁻¹.

EXAMPLE 6N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methylsulfonyl-3-thiophenesulfonamide

The crude 2-methylsulfonyl-3-thiophenesulfonyl isocyanate describedabove was dissolved in 100 ml of methylene chloride and 10 ml of thissolution (0.3 g of crude isocyanate) was added to 200 mg of4-methoxy-6-methyl-2-pyrimidinamine in methylene chloride containing afew crystals of DABCO. After stirring 3 days at room temperature, theprecipitate was filtered and washed with ether to afford 250 mg ofproduct, m.p. 204.5°-206° d. The IR spectrum showed a carbonylabsorption at 1680 cm⁻¹ indicative of a sulfonylurea.

Using the techniques described in Equations 1-20 and Examples 1-6, thefollowing compounds can be made by one skilled in the art.

                  TABLE IA                                                        ______________________________________                                         ##STR48##                                                                    R.sub.6        n          Z      Q                                            ______________________________________                                        CH.sub.3       0          CH     S                                            CH.sub.3       2          CH     S                                            CH.sub.3       0          N      S                                            CH.sub.3       2          N      S                                            C.sub.2 H.sub.5                                                                              0          CH     O                                            C.sub.2 H.sub.5                                                                              2          CH     S                                            C.sub.2 H.sub.5                                                                              0          N      S                                            C.sub.2 H.sub.5                                                                              2          N      S                                            n-C.sub.3 H.sub.7                                                                            0          CH     S                                            n-C.sub.3 H.sub.7                                                                            2          CH     O                                            n-C.sub.3 H.sub.7                                                                            0          N      S                                            n-C.sub.3 H.sub.7                                                                            2          N      S                                            i-C.sub.3 H.sub.7                                                                            0          CH     S                                            i-C.sub.3 H.sub.7                                                                            2          CH     S                                            i-C.sub.3 H.sub.7                                                                            0          N      S                                            i-C.sub.3 H.sub.7                                                                            2          N      S                                            CH.sub.2 CHCH.sub.2                                                                          0          CH     O                                            CH.sub.2 CHCH.sub.2                                                                          2          CH     S                                            CH.sub.2 CHCH.sub.2                                                                          0          N      S                                            CH.sub.2 CHCH.sub.2                                                                          2          N      S                                            i-C.sub.4 H.sub.9                                                                            0          CH     S                                            i-C.sub.4 H.sub.9                                                                            2          CH     S                                            i-C.sub.4 H.sub.9                                                                            0          N      S                                            i-C.sub.4 H.sub.9                                                                            2          N      S                                            n-C.sub.4 H.sub.9                                                                            0          CH     S                                            n-C.sub.4 H.sub.9                                                                            2          CH     S                                            n-C.sub.4 H.sub.9                                                                            0          N      O                                            n-C.sub.4 H.sub.9                                                                            2          N      S                                            CH.sub.2 CHCHCH.sub.3                                                                        2          CH     S                                            cyclopentyl    0          CH     S                                            cyclopentyl    2          CH     S                                            cyclopentyl    0          N      S                                            cyclopentyl    2          N      S                                            cyclopropylmethyl                                                                            0          CH     S                                            cyclopropylmethyl                                                                            2          CH     S                                            cyclopropylmethyl                                                                            0          N      S                                            cyclopropylmethyl                                                                            2          N      S                                            ______________________________________                                    

                  TABLE IB                                                        ______________________________________                                         ##STR49##                                                                    R.sub.6        n          Z      Q                                            ______________________________________                                        CH.sub.3       0          CH     S                                            CH.sub.3       2          CH     O                                            CH.sub.3       0          N      S                                            CH.sub.3       2          N      S                                            C.sub.2 H.sub.5                                                                              0          CH     S                                            C.sub.2 H.sub.5                                                                              2          CH     S                                            C.sub.2 H.sub.5                                                                              0          N      S                                            C.sub.2 H.sub.5                                                                              2          N      S                                            n-C.sub.3 H.sub.7                                                                            0          CH     S                                            n-C.sub.3 H.sub.7                                                                            2          CH     S                                            n-C.sub.3 H.sub.7                                                                            0          N      S                                            n-C.sub.3 H.sub.7                                                                            2          N      O                                            i-C.sub.3 H.sub.7                                                                            0          CH     S                                            i-C.sub.3 H.sub.7                                                                            2          CH     S                                            i-C.sub.3 H.sub.7                                                                            0          N      S                                            i-C.sub.3 H.sub.7                                                                            2          N      S                                            CH.sub.2 CHCH.sub.2                                                                          0          CH     S                                            CH.sub.2 CHCH.sub.2                                                                          2          CH     S                                            CH.sub.2 CHCH.sub.2                                                                          0          N      S                                            CH.sub.2 CHCH.sub.2                                                                          2          N      S                                            i-C.sub.4 H.sub.9                                                                            0          CH     S                                            i-C.sub.4 H.sub.9                                                                            2          CH     S                                            i-C.sub.4 H.sub.9                                                                            0          N      S                                            i-C.sub.4 H.sub.9                                                                            2          N      S                                            n-C.sub.4 H.sub.9                                                                            0          CH     S                                            n-C.sub.4 H.sub.9                                                                            2          CH     S                                            n-C.sub.4 H.sub.9                                                                            0          N      S                                            n-C.sub.4 H.sub.9                                                                            2          N      S                                            CH.sub.2 CHCHCH.sub.3                                                                        2          CH     S                                            cyclopentyl    0          CH     S                                            cyclopentyl    2          CH     O                                            cyclopentyl    0          N      S                                            cyclopentyl    2          N      S                                            cyclopropylmethyl                                                                            0          CH     S                                            cyclopropylmethyl                                                                            2          CH     S                                            cyclopropylmethyl                                                                            0          N      S                                            cyclopropylmethyl                                                                            2          N      S                                            ______________________________________                                    

                  TABLE IC                                                        ______________________________________                                         ##STR50##                                                                    R.sub.6        n          Z      Q                                            ______________________________________                                        CH.sub.3       0          CH     S                                            CH.sub.3       2          CH     S                                            CH.sub.3       0          N      S                                            CH.sub.3       2          N      S                                            C.sub.2 H.sub.5                                                                              0          CH     S                                            C.sub.2 H.sub.5                                                                              2          CH     S                                            C.sub.2 H.sub.5                                                                              0          N      S                                            C.sub.2 H.sub.5                                                                              2          N      S                                            n-C.sub.3 H.sub.7                                                                            0          CH     O                                            n-C.sub.3 H.sub.7                                                                            2          CH     S                                            n-C.sub.3 H.sub.7                                                                            0          N      S                                            n-C.sub.3 H.sub.7                                                                            2          N      S                                            i-C.sub.3 H.sub.7                                                                            0          CH     S                                            i-C.sub.2 H.sub.7                                                                            2          CH     S                                            i-C.sub.3 H.sub.7                                                                            0          N      S                                            i-C.sub.3 H.sub.7                                                                            2          N      S                                            CH.sub.2 CHCH.sub.2                                                                          0          CH     S                                            CH.sub.2 CHCH.sub.2                                                                          2          CH     O                                            CH.sub.2 CHCH.sub.2                                                                          0          N      S                                            CH.sub.2 CHCH.sub.2                                                                          2          N      S                                            i-C.sub.4 H.sub.9                                                                            0          CH     S                                            i-C.sub.4 H.sub.9                                                                            2          CH     S                                            i-C.sub.4 H.sub.9                                                                            0          N      S                                            i-C.sub.4 H.sub.9                                                                            2          N      S                                            n-C.sub.4 H.sub.9                                                                            0          CH     S                                            n-C.sub.4 H.sub.9                                                                            2          CH     S                                            n-C.sub.4 H.sub.9                                                                            0          N      S                                            n-C.sub.4 H.sub.9                                                                            2          N      S                                            CH.sub.2 CHCHCH.sub.3                                                                        2          CH     S                                            cyclopentyl    0          CH     O                                            cyclopentyl    2          CH     S                                            cyclopentyl    0          N      S                                            cyclopentyl    2          N      S                                            cyclopropylmethyl                                                                            0          CH     S                                            cyclopropylmethyl                                                                            2          CH     S                                            cyclopropylmethyl                                                                            0          N      S                                            cyclopropylmethyl                                                                            2          N      S                                            ______________________________________                                    

                  TABLE IIA                                                       ______________________________________                                         ##STR51##                                                                    R.sub.6              n     Q                                                  ______________________________________                                        CH.sub.3             0     S                                                  CH.sub.3             2     S                                                  C.sub.2 H.sub.5      0     S                                                  C.sub.2 H.sub.5      2     O                                                  n-C.sub.3 H.sub.7    0     S                                                  n-C.sub.3 H.sub.7    2     S                                                  i-C.sub.3 H.sub.7    0     S                                                  i-C.sub.3 H.sub.7    2     S                                                  CH.sub.2 CHCH.sub.2  0     S                                                  CH.sub.2 CHCH.sub.2  2     S                                                  n-C.sub.4 H.sub.9    0     S                                                  n-C.sub.4 H.sub.9    2     S                                                  i-C.sub.4 H.sub.9    0     O                                                  i-C.sub.4 H.sub.9    2     S                                                  cyclopentyl          0     O                                                  cyclopentyl          2     S                                                  cyclopropylmethyl    0     S                                                  cyclopropylmethyl    2     S                                                  CH.sub.2 CHCHCH.sub.3                                                                              2     S                                                  ______________________________________                                    

                  TABLE IIB                                                       ______________________________________                                         ##STR52##                                                                    R.sub.6              n     Q                                                  ______________________________________                                        CH.sub.3             0     S                                                  CH.sub.3             2     S                                                  C.sub.2 H.sub.5      0     O                                                  C.sub.2 H.sub.5      2     S                                                  n-C.sub.3 H.sub.7    0     S                                                  n-C.sub.3 H.sub.7    2     S                                                  i-C.sub.3 H.sub.7    0     S                                                  i-C.sub.3 H.sub.7    2     S                                                  CH.sub.2 CHCH.sub.2  0     S                                                  CH.sub.2 CHCH.sub.2  2     S                                                  n-C.sub.4 H.sub.9    0     O                                                  n-C.sub.4 H.sub.9    2     S                                                  i-C.sub.4 H.sub.9    0     S                                                  i-C.sub.4 H.sub.9    2     S                                                  cyclopentyl          0     S                                                  cyclopentyl          2     S                                                  cyclopropylmethyl    0     S                                                  cyclopropylmethyl    2     S                                                  CH.sub.2 CHCHCH.sub.3                                                                              2     S                                                  ______________________________________                                    

                  TABLE IIC                                                       ______________________________________                                         ##STR53##                                                                    R.sub.6              n     Q                                                  ______________________________________                                        CH.sub.3             0     S                                                  CH.sub.3             2     S                                                  C.sub.2 H.sub.5      0     S                                                  C.sub.2 H.sub.5      2     O                                                  n-C.sub.3 H.sub.7    0     S                                                  n-C.sub.3 H.sub.7    2     S                                                  i-C.sub.3 H.sub.7    0     S                                                  i-C.sub.3 H.sub.7    2     S                                                  CH.sub.2 CHCH.sub.2  0     S                                                  CH.sub.2 CHCH.sub.2  2     S                                                  n-C.sub.4 H.sub.9    0     S                                                  n-C.sub.4 H.sub.9    2     S                                                  i-C.sub.4 H.sub.9    0     S                                                  i-C.sub.4 H.sub.9    2     S                                                  cyclopentyl          0     O                                                  cyclopentyl          2     S                                                  cyclopropylmethyl    0     S                                                  cyclopropymethyl     2     S                                                  CH.sub.2 CHCHCH.sub.3                                                                              2     S                                                  ______________________________________                                    

                                      TABLE IIIA                                  __________________________________________________________________________     ##STR54##                                                                    R.sub.6   n R.sub.2                                                                           R.sub.3                                                                          R.sub.4                                                                           X   Y     Z  Q m.p. (°C.)                       __________________________________________________________________________    CH.sub.3  0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S 182-184°                         CH.sub.3  0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S 169-176°                         CH.sub.3  0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S 177-181° d                       CH.sub.3  0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub. 3 1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3 O                                                                          CH S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3 O                                                                        CH.sub.3 O                                                                          CH S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3 O                                                                          N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3 O                                                                        CH.sub.3 O                                                                          N  S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S 192-194°                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S 204-206°                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S 201-202°                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S 202-205°                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S 205-207°                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         C.sub.2 H.sub.5                                                                         0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       O H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S 127-128° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S 132-140° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S 134-138°                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S 153-156° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S 172-178° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub. 3                                                                          N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub. 3                                                                         CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          OCH.sub. 3                                                                        OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          OCh.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub. 4 H.sub.9                                                                      2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         CH.sub.2 CHCH.sub.2                                                                     2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub. 3                                                                          CH S                                         cyclopropylmethyl                                                                       2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  0 4-Cl                                                                              H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 5-CH.sub.3                                                                        H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 4-Br                                                                              H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         C.sub.2 H.sub.5                                                                     N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                  N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         Cl    N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         H     CH S                                         t-C.sub.4 H.sub.9                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCHCH.sub.3                                                                   2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         s-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         __________________________________________________________________________

                                      TABLE IIIB                                  __________________________________________________________________________     ##STR55##                                                                    R.sub.6   n R.sub.2                                                                           R.sub.3                                                                          R.sub.4                                                                           X   Y     Z  Q m.p. (°C.)                       __________________________________________________________________________    CH.sub.3  0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S 187-188°                         CH.sub.3  0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S 174-176°                         CH.sub.3  0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S 172-178°                         CH.sub.3  0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S 137°  d                          CH.sub.3  0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S 162-167°                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          OCH.sub. 3                                                                        OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3 O                                                                          CH O                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3 O                                                                        CH.sub.3 O                                                                          CH S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3 O                                                                          N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3 O                                                                        CH.sub.3 O                                                                          N  S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          Ch.sub.3                                                                            CH S 195-197°                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S 189-195°                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S 183-212°                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OCH.sub. 3                                                                          N  S 167-171°                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S 186-189° d                       CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         CH.sub.3  2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub. 2 H.sub.5                                                                        0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub. 3                                                                          CH O                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub. 3                                                                         CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S 175-179° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S 179-185° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S 195-201° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S 162-168° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S 172-176° d                       n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub. 3                                                                        OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub. 3                                                                         CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         cyclopentyl                                                                             2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub. 3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         i-C.sub.3 H.sub.7                                                                       2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  0 4-Cl                                                                              H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 5-CH.sub.3                                                                        H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 5-Br                                                                              H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         C.sub.2 H.sub.5                                                                     N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                  N  O                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         Cl    N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         H     CH S                                         t-C.sub.4 H.sub.9                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCHCH.sub.3                                                                   2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         s-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         __________________________________________________________________________

                                      TABLE IIIC                                  __________________________________________________________________________     ##STR56##                                                                    R.sub.6   n R.sub.2                                                                           R.sub.3                                                                          R.sub.4                                                                           X   Y     Z  Q m.p. (°C.)                       __________________________________________________________________________    CH.sub.3  0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         CH.sub.3  1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3 O                                                                          CH S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3 O                                                                        CH.sub.3 O                                                                          CH S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3                                                                          CH.sub.3 O                                                                          N  S                                         CH.sub.3  2 H   H  CH.sub.3 O                                                                        CH.sub.3 O                                                                        CH.sub.3 O                                                                          N  S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub. 3                                                                           CH O                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         CH.sub.3  2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub. 5                                                                        0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         C.sub.2 H.sub.5                                                                         1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         n-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       0 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       1 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH O                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub. 3                                                                          N  S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  O                                         cyclopentyl                                                                             2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         cyclopentyl                                                                             2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopropylmethyl                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         cyclopropylmethyl                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         n-C.sub.4 H.sub.9                                                                       2 H   H  CH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         CH.sub.3  2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         C.sub.2 H.sub.5                                                                         2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         i-C.sub.3 H.sub.7                                                                       2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          CH.sub.3                                                                            CH S                                         CH.sub.2 CHCH.sub.2                                                                     2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           N  S                                         cyclopentyl                                                                             2 H   CH.sub.3                                                                         H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         cyclopropylmethyl                                                                       2 H   CH.sub.3                                                                         H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.3  0 2-Cl                                                                              H  H   CH.sub.3                                                                          OCH.sub.3                                                                           CH S                                         C.sub.2 H.sub.5                                                                         2 5-CH.sub.3                                                                        H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         n-C.sub.3 H.sub.7                                                                       2 2-Br                                                                              H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                         CH.sub.3  2 H   H  H   CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    CH S                                         C.sub.2 H.sub.5                                                                         1 H   H  H   OCH.sub.3                                                                         C.sub.2 H.sub.5                                                                     N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                  N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         Cl    N  S                                         CH.sub.3  2 H   H  H   OCH.sub.3                                                                         H     CH S                                         t-C.sub.4 H.sub.9                                                                       0 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         CH.sub.2 CHCHCH.sub.3                                                                   2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         i-C.sub.4 H.sub.9                                                                       2 H   H  H   CH.sub.3                                                                          OCH.sub.3                                                                           N  S                                         s-C.sub.4 H.sub.9                                                                       2 H   H  H   OCH.sub.3                                                                         OCH.sub.3                                                                           CH S                                         __________________________________________________________________________

                  TABLE IVA                                                       ______________________________________                                         ##STR57##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                             R.sub.4                                                                             Y.sub.1                                                                              Q                                ______________________________________                                        CH.sub.3 0       H        H     H     H      S                                CH.sub.3 0       H        H     H     Cl     S                                CH.sub.3 0       H        H     H     CH.sub.3                                                                             S                                CH.sub.3 0       H        H     H     OCH.sub.3                                                                            S                                CH.sub.3 1       4-Cl     H     H     CH.sub.3                                                                             S                                CH.sub.3 2       H        H     H     H      O                                CH.sub.3 2       H        H     H     Cl     S                                CH.sub.3 2       H        H     CH.sub.3                                                                            CH.sub.3                                                                             S                                CH.sub.3 2       H        H     H     OCH.sub.3                                                                            S                                CH.sub.3 1       4-Br     H     H     OCH.sub.3                                                                            S                                CH.sub. 3                                                                              2       5-CH.sub.3                                                                             H     H     CH.sub.3                                                                             S                                CH.sub.3 2       H        CH.sub.3                                                                            H     H      S                                C.sub.2 H.sub.5                                                                        0       H        H     CH.sub.3                                                                            H      S                                C.sub.2 H.sub.5                                                                        0       H        H     H     OCH.sub.3                                                                            S                                C.sub.2 H.sub.5                                                                        2       5-Cl     H     H     H      O                                i-C.sub.3 H.sub.7                                                                      2       H        H     H     CH.sub.3                                                                             S                                n-Bu     2       H        H     H     OCH.sub.3                                                                            S                                CH.sub.2 CHCH                                                                          1       H        H     H     OCH.sub.3                                                                            S                                n-C.sub.3 H.sub.7                                                                      0       H        H     H     CH.sub.3                                                                             S                                 ##STR58##                                                                             2       H        H     H     OCH.sub.3                                                                            S                                 ##STR59##                                                                             2       5-Br     H     H     OCH.sub.3                                                                            S                                 ##STR60##                                                                             2       H        H     H     CH.sub.3                                                                             S                                ______________________________________                                    

                  TABLE IVB                                                       ______________________________________                                         ##STR61##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                             R.sub.4                                                                             Y.sub.1                                                                              Q                                ______________________________________                                        CH.sub.3 0       H        H     H     H      S                                CH.sub.3 0       H        H     H     Cl     S                                CH.sub.3 0       H        H     H     CH.sub.3                                                                             S                                CH.sub.3 0       H        H     H     OCH.sub.3                                                                            S                                CH.sub.3 1       4-Cl     H     H     CH.sub.3                                                                             S                                CH.sub.3 2       H        H     H     H      S                                CH.sub.3 2       H        H     H     Cl     S                                CH.sub.3 2       H        H     CH.sub.3                                                                            CH.sub.3                                                                             S                                CH.sub.3 2       H        H     H     OCH.sub.3                                                                            S                                CH.sub.3 1       4-Br     H     H     OCH.sub.3                                                                            S                                CH.sub. 3                                                                              2       4-CH.sub.3                                                                             H     H     CH.sub.3                                                                             S                                CH.sub.3 2       H        CH.sub.3                                                                            H     H      O                                C.sub.2 H.sub.5                                                                        0       H        H     CH.sub.3                                                                            H      S                                C.sub.2 H.sub.5                                                                        0       H        H     H     OCH.sub.3                                                                            S                                C.sub.2 H.sub.5                                                                        2       5-Cl     H     H     H      S                                i-C.sub.3 H.sub.7                                                                      2       H        H     H     CH.sub.3                                                                             S                                n-Bu     2       H        H     H     OCH.sub.3                                                                            S                                CH.sub.2 CHCH                                                                          1       H        H     H     OCH.sub.3                                                                            S                                n-C.sub.3 H.sub.7                                                                      0       H        H     H     CH.sub.3                                                                             S                                 ##STR62##                                                                             2       H        H     H     OCH.sub.3                                                                            S                                 ##STR63##                                                                             2       5-Br     H     H     OCH.sub.3                                                                            S                                 ##STR64##                                                                             2       H        H     H     CH.sub.3                                                                             S                                ______________________________________                                    

                  TABLE IVC                                                       ______________________________________                                         ##STR65##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                             R.sub.4                                                                             Y.sub.1                                                                              Q                                ______________________________________                                        CH.sub.3 0       H        H     H     H      S                                CH.sub.3 0       H        H     H     Cl     S                                CH.sub.3 0       H        H     H     CH.sub.3                                                                             S                                CH.sub.3 0       H        H     H     OCH.sub.3                                                                            S                                CH.sub.3 1       2-Cl     H     H     CH.sub.3                                                                             O                                CH.sub.3 2       H        H     H     H      O                                CH.sub.3 2       H        H     H     Cl     O                                CH.sub.3 2       H        H     CH.sub.3                                                                            CH.sub.3                                                                             S                                CH.sub.3 2       H        H     H     OCH.sub.3                                                                            S                                CH.sub.3 1       2-Br     H     H     OCH.sub.3                                                                            S                                CH.sub.3 2       2-CH.sub.3                                                                             H     H     CH.sub.3                                                                             S                                CH.sub.3 2       H        CH.sub.3                                                                            H     H      S                                C.sub.2 H.sub.5                                                                        0       H        H     CH.sub.3                                                                            H      S                                C.sub.2 H.sub.5                                                                        0       H        H     H     OCH.sub.3                                                                            S                                C.sub.2 H.sub.5                                                                        2       5-Cl     H     H     H      S                                i-C.sub.3 H.sub.7                                                                      2       H        H     H     CH.sub.3                                                                             S                                n-Bu     2       H        H     H     OCH.sub.3                                                                            S                                CH.sub.2 CHCH                                                                          1       H        H     H     OCH.sub.3                                                                            S                                n-C.sub.3 H.sub.7                                                                      0       H        H     H     CH.sub.3                                                                             S                                 ##STR66##                                                                             2       H        H     H     OCH.sub.3                                                                            S                                 ##STR67##                                                                             2       5-Br     H     H     OCH.sub.3                                                                            S                                 ##STR68##                                                                             2       H        H     H     CH.sub.3                                                                             S                                ______________________________________                                    

                  TABLE VA                                                        ______________________________________                                         ##STR69##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                 ______________________________________                                        CH.sub.3 0       H        H    H      H     S                                 CH.sub.3 0       H        H    H      Cl    S                                 CH.sub.3 0       H        H    H      CH.sub.3                                                                            S                                 CH.sub.3 0       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       4-Cl     H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        H    H      H     S                                 CH.sub.3 2       H        H    H      Cl    S                                 CH.sub.3 2       H        H    CH.sub.3                                                                             CH.sub.3                                                                            S                                 CH.sub.3 2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       4-Br     H    H      OCH.sub.3                                                                           S                                 CH.sub.3 2       5-CH.sub.3                                                                             H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        CH.sub.3                                                                           H      H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    CH.sub.3                                                                             H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    H      OCH.sub.3                                                                           S                                 C.sub.2 H.sub.5                                                                        2       5-Cl     H    H      H     O                                 i-C.sub.3 H.sub.7                                                                      2       H        H    H      CH.sub.3                                                                            S                                 n-Bu     2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.2 CHCH                                                                          1       H        H    H      OCH.sub.3                                                                           S                                 n-C.sub.3 H.sub.7                                                                      0       H        H    H      CH.sub.3                                                                            S                                  ##STR70##                                                                             2       H        H    H      OCH.sub.3                                                                           O                                  ##STR71##                                                                             2       4-Br     H    H      OCH.sub.3                                                                           S                                  ##STR72##                                                                             2       H        H    H      CH.sub.3                                                                            S                                 ______________________________________                                    

                  TABLE VB                                                        ______________________________________                                         ##STR73##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                 ______________________________________                                        CH.sub.3 0       H        H    H      H     S                                 CH.sub.3 0       H        H    H      Cl    S                                 CH.sub.3 0       H        H    H      CH.sub.3                                                                            S                                 CH.sub.3 0       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       4-Cl     H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        H    H      H     S                                 CH.sub.3 2       H        H    H      Cl    S                                 CH.sub.3 2       H        H    CH.sub.3                                                                             CH.sub.3                                                                            O                                 CH.sub.3 2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       5-Br     H    H      OCH.sub.3                                                                           S                                 CH.sub.3 2       5-CH.sub.3                                                                             H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        CH.sub.3                                                                           H      H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    CH.sub.3                                                                             H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    H      OCH.sub.3                                                                           S                                 C.sub.2 H.sub.5                                                                        2       4-Cl     H    H      H     S                                 i-C.sub.3 H.sub.7                                                                      2       H        H    H      CH.sub.3                                                                            S                                 n-Bu     2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.2 CHCH                                                                          1       H        H    H      OCH.sub.3                                                                           S                                 n-C.sub.3 H.sub.7                                                                      0       H        H    H      CH.sub.3                                                                            S                                  ##STR74##                                                                             2       H        H    H      OCH.sub.3                                                                           S                                  ##STR75##                                                                             2       4-Br     H    H      OCH.sub.3                                                                           O                                  ##STR76##                                                                             2       H        H    H      CH.sub.3                                                                            O                                 ______________________________________                                    

                  TABLE VC                                                        ______________________________________                                         ##STR77##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                 ______________________________________                                        CH.sub.3 0       H        H    H      H     S                                 CH.sub.3 0       H        H    H      Cl    O                                 CH.sub.3 0       H        H    H      CH.sub.3                                                                            O                                 CH.sub.3 0       H        H    H      OCH.sub.3                                                                           O                                 CH.sub.3 1       5-Cl     H    H      CH.sub.3                                                                            O                                 CH.sub.3 2       H        H    H      H     O                                 CH.sub.3 2       H        H    H      Cl    O                                 CH.sub.3 2       H        H    CH.sub.3                                                                             CH.sub.3                                                                            O                                 CH.sub.3 2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       5-Br     H    H      OCH.sub.3                                                                           S                                 CH.sub.3 2       2-CH.sub. 3                                                                            H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        CH.sub.3                                                                           H      H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    CH.sub.3                                                                             H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    H      OCH.sub.3                                                                           S                                 C.sub.2 H.sub.5                                                                        2       2-Cl     H    H      H     S                                 i-C.sub.3 H.sub.7                                                                      2       H        H    H      CH.sub.3                                                                            S                                 n-Bu     2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.2 CHCH                                                                          1       H        H    H      OCH.sub.3                                                                           S                                 n-C.sub.3 H.sub.7                                                                      0       H        H    H      CH.sub.3                                                                            S                                  ##STR78##                                                                             2       H        H    H      OCH.sub.3                                                                           S                                  ##STR79##                                                                             2       2-Br     H    H      OCH.sub.3                                                                           S                                  ##STR80##                                                                             2       H        H    H      CH.sub.3                                                                            S                                 ______________________________________                                    

                  TABLE VIA                                                       ______________________________________                                         ##STR81##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                 ______________________________________                                        CH.sub.3 0       H        H    H      H     O                                 CH.sub.3 0       H        H    H      Cl    S                                 CH.sub.3 0       H        H    H      CH.sub.3                                                                            S                                 CH.sub.3 0       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       4-Cl     H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        H    H      H     S                                 CH.sub.3 2       H        H    H      Cl    S                                 CH.sub.3 2       H        H    CH.sub.3                                                                             CH.sub.3                                                                            S                                 CH.sub.3 2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       5-Br     H    H      OCH.sub.3                                                                           S                                 CH.sub.3 2       4-CH.sub.3                                                                             H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        CH.sub.3                                                                           H      H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    CH.sub.3                                                                             H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    H      OCH.sub.3                                                                           S                                 C.sub.2 H.sub.5                                                                        2       5-Cl     H    H      H     S                                 i-C.sub.3 H.sub.7                                                                      2       H        H    H      CH.sub.3                                                                            S                                 n-Bu     2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.2 CHCH                                                                          1       H        H    H      OCH.sub.3                                                                           S                                 n-C.sub.3 H.sub.7                                                                      0       H        H    H      CH.sub.3                                                                            S                                  ##STR82##                                                                             2       H        H    H      OCH.sub.3                                                                           O                                  ##STR83##                                                                             2       4-Br     H    H      OCH.sub.3                                                                           O                                  ##STR84##                                                                             2       H        H    H      CH.sub.3                                                                            O                                 ______________________________________                                    

                  TABLE VIB                                                       ______________________________________                                         ##STR85##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                 ______________________________________                                        CH.sub.3 0       H        H    H      H     S                                 CH.sub.3 0       H        H    H      Cl    S                                 CH.sub.3 0       H        H    H      CH.sub.3                                                                            S                                 CH.sub.3 0       H        H    H      OCH.sub.3                                                                           O                                 CH.sub.3 1       5-Cl     H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        H    H      H     S                                 CH.sub.3 2       H        H    H      Cl    S                                 CH.sub.3 2       H        H    CH.sub.3                                                                             CH.sub.3                                                                            S                                 CH.sub.3 2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       5-Br     H    H      OCH.sub.3                                                                           S                                 CH.sub.3 2       4-CH.sub.3                                                                             H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        CH.sub.3                                                                           H      H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    CH.sub.3                                                                             H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    H      OCH.sub.3                                                                           S                                 C.sub.2 H.sub.5                                                                        2       4-Cl     H    H      H     O                                 i-C.sub.3 H.sub.7                                                                      2       H        H    H      CH.sub.3                                                                            S                                 n-Bu     2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.2 CHCH                                                                          1       H        H    H      OCH.sub.3                                                                           S                                 n-C.sub.3 H.sub.7                                                                      0       H        H    H      CH.sub.3                                                                            S                                  ##STR86##                                                                             2       H        H    H      OCH.sub.3                                                                           S                                  ##STR87##                                                                             2       5-Br     H    H      OCH.sub.3                                                                           S                                  ##STR88##                                                                             2       H        H    H      CH.sub.3                                                                            S                                 ______________________________________                                    

                  TABLE VIC                                                       ______________________________________                                         ##STR89##                                                                    R.sub.6  n       R.sub.2  R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                 ______________________________________                                        CH.sub.3 0       H        H    H      H     S                                 CH.sub.3 0       H        H    H      Cl    S                                 CH.sub.3 0       H        H    H      CH.sub.3                                                                            S                                 CH.sub.3 0       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.3 1       5-Cl     H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        H    H      H     S                                 CH.sub.3 2       H        H    H      Cl    S                                 CH.sub.3 2       H        H    CH.sub.3                                                                             CH.sub.3                                                                            O                                 CH.sub.3 2       H        H    H      OCH.sub.3                                                                           O                                 CH.sub.3 1       2-Br     H    H      OCH.sub. 3                                                                          O                                 CH.sub.3 2       5-CH.sub.3                                                                             H    H      CH.sub.3                                                                            S                                 CH.sub.3 2       H        CH.sub.3                                                                           H      H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    CH.sub.3                                                                             H     S                                 C.sub.2 H.sub.5                                                                        0       H        H    H      OCH.sub.3                                                                           S                                 C.sub.2 H.sub.5                                                                        2       5-Cl     H    H      H     S                                 i-C.sub.3 H.sub.7                                                                      2       H        H    H      CH.sub.3                                                                            S                                 n-Bu     2       H        H    H      OCH.sub.3                                                                           S                                 CH.sub.2 CHCH                                                                          1       H        H    H      OCH.sub.3                                                                           S                                 n-C.sub.3 H.sub.7                                                                      0       H        H    H      CH.sub.3                                                                            S                                  ##STR90##                                                                             2       H        H    H      OCH.sub.3                                                                           S                                  ##STR91##                                                                             2       2-Br     H    H      OCH.sub.3                                                                           S                                  ##STR92##                                                                             2       H        H    H      CH.sub.3                                                                            O                                 ______________________________________                                    

                  TABLE VIIA                                                      ______________________________________                                         ##STR93##                                                                    R.sub.6    n     R.sub.2                                                                              R.sub.3                                                                            R.sub.4                                                                            X     Y.sub.2                                                                             Q                               ______________________________________                                        CH.sub.3   2     H      H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            O                               CH.sub.3   0     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               CH.sub.3   0     5-Cl   H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub. 3                                                                           OCH.sub.3                                                                           S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           O                               n-C.sub.3 H.sub.7                                                                        0     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     4-Br   H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        0     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.2 CHCH.sub.2                                                                      0     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               ______________________________________                                    

                  TABLE VIIB                                                      ______________________________________                                         ##STR94##                                                                    R.sub.6    n     R.sub.2                                                                              R.sub.3                                                                            R.sub.4                                                                            X     Y.sub.2                                                                             Q                               ______________________________________                                        CH.sub.3   2     H      H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            O                               CH.sub.3   0     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               CH.sub.3   0     5-CH.sub.3                                                                           H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           O                               n-C.sub.3 H.sub.7                                                                        0     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     4-Br   H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        0     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.2 CHCH.sub.2                                                                      0     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               ______________________________________                                    

                  TABLE VIIC                                                      ______________________________________                                         ##STR95##                                                                    R.sub.6    n     R.sub.2                                                                              R.sub.3                                                                            R.sub.4                                                                            X     Y.sub.2                                                                             Q                               ______________________________________                                        CH.sub.3   2     H      H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            O                               CH.sub.3   0     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               CH.sub.3   0     2-Cl   H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           O                               n-C.sub.3 H.sub.7                                                                        0     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     5-CH.sub.3                                                                           H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        0     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.2 CHCH.sub.2                                                                      0     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               ______________________________________                                    

                  TABLE VIIIA                                                     ______________________________________                                         ##STR96##                                                                    R.sub.6    n     R.sub.2                                                                              R.sub.3                                                                            R.sub.4                                                                            X     Y.sub.2                                                                             Q                               ______________________________________                                        CH.sub.3   2     H      H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            O                               CH.sub.3   0     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               CH.sub.3   0     4-Cl   H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub. 5                                                                         2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           O                               n-C.sub.3 H.sub.7                                                                        0     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     5-CH.sub.3                                                                           H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        0     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.2 CHCH.sub.2                                                                      0     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               ______________________________________                                    

                  TABLE VIIIB                                                     ______________________________________                                         ##STR97##                                                                    R.sub.6    n     R.sub.2                                                                              R.sub.3                                                                            R.sub.4                                                                            X     Y.sub.2                                                                             Q                               ______________________________________                                        CH.sub.3   2     H      H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            O                               CH.sub.3   0     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               CH.sub.3   0     4-Br   H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub. 5                                                                         2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           O                               n-C.sub.3 H.sub.7                                                                        0     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     5-Cl   H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        0     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.2 CHCH.sub.2                                                                      0     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               ______________________________________                                    

                  TABLE VIIIC                                                     ______________________________________                                         ##STR98##                                                                    R.sub.6    n     R.sub.2                                                                              R.sub.3                                                                            R.sub.4                                                                            X     Y.sub.2                                                                             Q                               ______________________________________                                        CH.sub.3   2     H      H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               CH.sub.3   2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            O                               CH.sub.3   0     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               CH.sub.3   0     5-Cl   H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               C.sub.2 H.sub.5                                                                          2     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               n-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           O                               n-C.sub.3 H.sub.7                                                                        0     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     2-Cl   H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        0     H      H    H    CH.sub.3                                                                            OCH.sub.3                                                                           S                               n-C.sub.4 H.sub.9                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    CH.sub.3                                                                            CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               i-C.sub.3 H.sub.7                                                                        2     H      H    H    OCH.sub.3                                                                           OCH.sub.3                                                                           S                               CH.sub.2 CHCH.sub.2                                                                      0     H      H    H    OCH.sub.3                                                                           CH.sub.3                                                                            S                               ______________________________________                                    

                  TABLE IXA                                                       ______________________________________                                         ##STR99##                                                                    R.sub.6  n     R.sub.2   R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                  ______________________________________                                        CH.sub.3 2     H         CH.sub.3                                                                           H      CH.sub.3                                                                            S                                  CH.sub.3 2     H         H    CH.sub.3                                                                             OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      CH.sub.3                                                                            S                                  CH.sub.3 2     H         H    H      OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      CH.sub.3                                                                            O                                  CH.sub.3 0     4-CH.sub.3                                                                              H    H      OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      OCH.sub.3                                                                           S                                  CH.sub.3 0     H         H    H      OCH.sub.3                                                                           S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      OCH.sub.3                                                                           S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      OCH.sub.3                                                                           S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      0     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.4 H.sub.7                                                                      2     H         H    H      OCH.sub.3                                                                           S                                  n-C.sub.4 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.4 H.sub.7                                                                      2     5-CH.sub.3                                                                              H    H      OCH.sub.3                                                                           S                                  i-C.sub.3 H.sub.7                                                                      0     H         H    H      OCH.sub.3                                                                           O                                  i-C.sub.3 H.sub.7                                                                      2     H         H    H      OCH.sub.3                                                                           S                                  i-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  cyclopentyl                                                                            2     H         H    H      OCH.sub.3                                                                           S                                  ______________________________________                                    

                  TABLE IXB                                                       ______________________________________                                         ##STR100##                                                                   R.sub.6  n     R.sub.2   R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                  ______________________________________                                        CH.sub.3 2     H         CH.sub.3                                                                           H      CH.sub.3                                                                            S                                  CH.sub.3 2     H         H    CH.sub.3                                                                             OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      CH.sub.3                                                                            S                                  CH.sub.3 2     H         H    H      OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      CH.sub.3                                                                            O                                  CH.sub.3 0     4-CH.sub.3                                                                              H    H      OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      OCH.sub.3                                                                           S                                  CH.sub.3 0     H         H    H      OCH.sub.3                                                                           S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      OCH.sub.3                                                                           S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      OCH.sub. 3                                                                          S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      0     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.4 H.sub.7                                                                      2     H         H    H      OCH.sub.3                                                                           S                                  n-C.sub.4 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.4 H.sub.7                                                                      2     5-Br      H    H      OCH.sub.3                                                                           S                                  i-C.sub.3 H.sub.7                                                                      0     H         H    H      OCH.sub.3                                                                           O                                  i-C.sub.3 H.sub.7                                                                      2     H         H    H      OCH.sub.3                                                                           S                                  i-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  cyclopentyl                                                                            2     H         H    H      OCH.sub.3                                                                           S                                  ______________________________________                                    

                  TABLE IXC                                                       ______________________________________                                         ##STR101##                                                                   R.sub.6  n     R.sub.2   R.sub.3                                                                            R.sub.4                                                                              Y.sub.1                                                                             Q                                  ______________________________________                                        CH.sub.3 2     H         CH.sub.3                                                                           H      CH.sub.3                                                                            S                                  CH.sub.3 2     H         H    CH.sub.3                                                                             OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      CH.sub.3                                                                            S                                  CH.sub.3 2     H         H    H      OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      CH.sub.3                                                                            O                                  CH.sub.3 0     2-CH.sub.3                                                                              H    H      OCH.sub.3                                                                           S                                  CH.sub.3 2     H         H    H      OCH.sub.3                                                                           S                                  CH.sub.3 0     H         H    H      OCH.sub.3                                                                           S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      OCH.sub.3                                                                           S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      OCH.sub.3                                                                           S                                  C.sub.2 H.sub.5                                                                        2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      0     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.4 H.sub.7                                                                      2     H         H    H      OCH.sub.3                                                                           S                                  n-C.sub.4 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  n-C.sub.4 H.sub.7                                                                      2     5-Cl      H    H      OCH.sub.3                                                                           S                                  i-C.sub.3 H.sub.7                                                                      0     H         H    H      OCH.sub.3                                                                           O                                  i-C.sub.3 H.sub.7                                                                      2     H         H    H      OCH.sub.3                                                                           S                                  i-C.sub.3 H.sub.7                                                                      2     H         H    H      CH.sub.3                                                                            S                                  cyclopentyl                                                                            2     H         H    H      OCH.sub.3                                                                           S                                  ______________________________________                                    

FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

                  TABLE VII                                                       ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J. but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powders anthe denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preferred granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 7

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                         80%                                               (methylsulfonyl)-3-thiophenesulfonamide                                       sodium alkylnaphthalenesulfonate                                                                          2%                                                sodium ligninsulfonate      2%                                                synthetic amorphous silica  3%                                                kaolinite                   13%                                               ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 8

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                         50%                                               (methylsulfonyl)-3-thiophenesulfonamide                                       sodium alkylnaphthalenesulfonate                                                                          2%                                                low viscosity methyl cellulose                                                                            2%                                                diatomaceous earth          46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 9

    ______________________________________                                        Granule                                                                       ______________________________________                                        Wettable Powder of ExampIe 8                                                                             5%                                                 attapulgite granules       95%                                                (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 10

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-                                                     25%                                             (methylsulfonyl)-3-thiophenesulfonamide                                       anhydrous sodium sulfate      10%                                             crude calcium ligninsulfonate 5%                                              sodium alkylnaphthalenesulfonate                                                                            1%                                              calcium/magnesium bentonite   59%                                             ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on U.S.S. No.40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 11

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-                                                     25%                                             (methylsulfonyl)-3-thiophenesulfonamide                                       polyoxyethylene sorbitol hexaoleate                                                                         5%                                              highly aliphatic hydrocarbon oil                                                                            70%                                             ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 12

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                         20%                                               (methylsulfonyl)-3-thiophenesulfonamide                                       sodium alkylnaphthalenesulfonate                                                                          4%                                                sodium ligninsulfonate      4%                                                low viscosity methyl cellulose                                                                            3%                                                attapulgite                 69%                                               ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 13

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-                                                     1%                                              (methylsulfonyl)-3-thiophenesulfonamide                                       N,N--dimethylformamide        9%                                              attapulgite granules          90%                                             (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 14

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                         40%                                               (methylsulfonyl)-3-thiophenesulfonamide                                       polyacrylic acid thickener  0.3%                                              dodecylphenol polyethylene glycol ether                                                                   0.5%                                              disodium phosphate          1%                                                monosodium phosphate        0.5%                                              polyvinyl alcohol           1.0%                                              water                       56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 15

    ______________________________________                                        Solution                                                                      ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                             (methylsulfonyl)-3-thiophenesulfonamide,                                      sodium salt                 5%                                                water                       95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 16

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-                                                   0.1%                                              (methylsulfonyl)-3-thiophenesulfonamide                                       attapulgite granules        99.9%                                             (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 17

    ______________________________________                                        Granule                                                                       ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                         80%                                               (methylsulfonyl)-3-thiophenesulfonamide                                       wetting agent               1%                                                crude ligninsulfonate salt (containing                                                                    10%                                               5-20% of the natural sugars)                                                  attapulgite clay            9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 18

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-                                                     99%                                             (methylsulfonyl)-3-thiophenesulfonamide                                       silica aerogel                0.5%                                            synthetic amorphous silica    0.5%                                            ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 19

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                         90%                                               (methylsulfonyl)-3-thiophenesulfonamide                                       dioctyl sodium sulfosuccinate                                                                             0.1%                                              synthetic fine silica       9.9%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 20

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                         40%                                               (methylsulfonyl)-3-thiophenesulfonamide                                       sodium ligninsulfonate      20%                                               montmorillonite clay        40%                                               ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 21

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N--[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-                                                     35%                                             (methylsulfonyl)-3-thiophenesulfonamide                                       blend of polyalcohol carboxylic                                                                             6%                                              esters and oil soluble petroleum                                              sulfonates                                                                    xylene                        59%                                             ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 22

    ______________________________________                                        Dust                                                                          ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-                                                           10%                                             (methylsulfonyl)-3-thiophenesulfonamide                                       attapulgite                   10%                                             Pyrophyllite                  80%                                             ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

UTILITY

The compounds of the present invention are active herbicides. They haveutility for broad-spectrum pre- and/or post-emergence weed control inareas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,oil-well sites, drive-in theaters, around billboards, highway andrailroad structures. By properly selecting rate, time and method ofapplication, compounds of this invention may also be used to modifyplant growth beneficially, and also to selectively control weeds incrops such as wheat, barley, corn and soybeans.

The precise amount of the compounds of Formula I to be used in any givensituation will vary according to the particular end result desired, theamount of foliage present, the weeds to be controlled, the crop speciesinvolved, the soil type, the formulation and mode of application,weather conditions, etc. Since so many variables play a role, it is notpossible to state a rate of application suitable for all situations.Broadly speaking, the compounds of this invention are used at levels ofabout 0.01 to 20 kg/ha with a preferred range of 0.03 to 10 kg/ha. Ingeneral, the higher rates of application from within this range will beselected for adverse conditions or where extended persistence in soil isdesired.

The compounds of Formula I may be combined with other herbicides and areparticularly useful in combination with the ureas: such as3-(3,4-dichlorophenyl)-1,1-dimethylurea (diuron); the triazines: such as2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine (atrazine); theuracils: such as 5-bromo-3-sec-butyl-6-methyluracil (bromacil);N-(phosponomethyl)glycine (glyphosate);3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione(hexazinone); N,N-dimethyl-2,2-diphenylacetamide (diphenamid);2,4-dichlorophenoxyacetic acid (2,4-D) (and closely related compounds);4-chloro-2-butynyl-3-chlorophenylcarbamate (barban);S-(2,3-dichloroallyl)-diisopropylthiocarbamate (diallate);S-(2,3,3-trichloroallyl-diisopropylthiocarbamate (triallate);1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquatmethyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate(diclofop methyl);4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one(metribuzin); 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (linuron);3-isopropyl-1H-2,1,3-benzothiodiazin-4(3H)-one-2,2-dioxide (bentazon);α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (trifluralin);1,1'-dimethyl-4,4'-bipyridinium ion (paraquat); monosodiummethanearsonate (MSMA); 2-chloro-2',6'-diethyl(methoxymethyl)acetanilide (alachlor);1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)-urea (fluometuron); and5-[2-chloro-4-trifluoromethyl)phenoxy]-2-nitrobenzoic acid, methyl ester(acifluorfen-methyl).

The activity of these compounds was discovered in greenhouse tests. Thetests are described and data resulting from them are shown below. Itwill be seen that certain of the compounds tested provide effective weedcontrol at rates of application which are non-injurious to wheat, corn,or soybeans.

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory(Ipomoea sp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice,wheat and nutsedge tubers (Cyperus rotundus) were planted in a growthmedium and treated pre-emergence with the chemicals dissolved in anon-phytotoxic solvent. At the same time, cotton having five leaves(including cotyledonary ones), bush beans with the second trifoliateleaf expanding, crabgrass and barnyardgrass with two leaves, wild oatswith one leaf, cassia with three leaves (including cotyledonary ones),morningglory and cocklebur with four leaves (including the cotyledonaryones), sorghum with three leaves, corn with three leaves, soybean withtwo cotyledonary leaves, rice with two leaves, wheat with two leaves,and nutsedge with three to five leaves were sprayed. Treated plants andcontrols were maintained in a greenhouse for sixteen days, then allspecies were compared to controls and visually rated for response totreatment.

The ratings are based on a numerical scale extending from 0=no injury,to 10=complete kill. The accompanying descriptive symbols have thefollowing meanings:

G=growth retardation

C=chlorosis or necrosis

E=emergence inhibition

H=formative effects

6Y=abscised buds or flowers

U=unusual pigmentation

X=axillary stimulation

P=terminal bud killed

D=defoliation

A=growth acceleration ##STR102##

                                      TABLE A                                     __________________________________________________________________________    Rate kg/ha  .05   .05   .05   .05   .05  .05   .05  .05   .05                 __________________________________________________________________________    POST-EMERGENCE                                                                            Cmpd. 1                                                                             Cmpd. 2                                                                             Cmpd. 3                                                                             Cmpd. 4                                                                             Cmpd. 5                                                                            Cmpd. 6                                                                             Cmpd. 7                                                                            Cmpd.                                                                               Cmpd.               __________________________________________________________________________                                                              9                   Bush bean   9C    2C,9G,6Y                                                                            9C    8C    9C   9C    9C   10G,6C                                                                              10C                 Cotton      9C    --    2U,5C,9G                                                                            9C    9C   5C,9G 6C,9G                                                                              10G,8C                                                                              10C                 Sorghum     2U,9G 2C,9H 6U,9G 5U    7U,9G                                                                              4U,9G 2U,9G                                                                              10C   10C                 Corn        3U,9G 0     7U,9C 9C    5C,9G                                                                              9C    2U,8H                                                                              10G,3C                                                                              10C                 Soybean     9C    2C,8G 9C    9C    9C   9C    4C,8G                                                                              10G,3C                                                                              10C                 Wheat       1C,9G 2C,9G 3U,9G 2C    2C,9G                                                                              3G    0    10G,2C                                                                              10G,2C              Wild Oats   5C,9G 2C,9G 3C,8G 5C    2C,9G                                                                              2G    0    10G,9C                                                                              10G,4C              Rice        9C    4C,9G 9C    9C    9C   5C,9G 4C,9G                                                                              10G,5C                                                                              10G,6C              Barnyardgrass                                                                             6C,9H 2C,5H 9C    9C    9C   3C,9H 9H   10G,9C                                                                              10G,9C              Crabgrass   8G    2C,6G 2C,8G 5C,5C,9G                                                                            3C,9G                                                                              5G    10G,5C                                                                             10G,5C                    Morningglory                                                                              10C   3C,8H 3C,9H 9C    5C,9G                                                                              1C,5G 2C,3G                                                                              10G,7C                                                                              10G,5C              Cocklebur   9C    2C,6G 10C   10C   5C,9G                                                                              9C    4G   10G   10C                 Cassia      6C,9G 3C,6H 6C,9G 9C    9C   3C,7G 2C,5G                                                                              10G,9C                                                                              10G,4C              Nutsedge    3C,9G 0     3C,8G 3C    9C   8G    1C   10G,3C                                                                              9G,2C               __________________________________________________________________________                Cmpd. 10                                                                            Cmpd. 11                                                                            Cmpd. 12                                                                            Cmpd. 13                                                                            Cmpd. 14                                                                           Cmpd. 15                                                                            Cmpd. 16                                                                           Cmpd.                                                                               Cmpd.               __________________________________________________________________________                                                              18                  Bush bean   9G,9C 9G    10G,3C                                                                              10G,6C                                                                              9C   9D,9G,6Y                                                                            1C   4C,9G,6Y                                                                            9C                  Cotton      10C   8G,2C 3G    10G,5C                                                                              9C   6C,9G 4C,6H                                                                              4C,4H,9G                                                                            9C                  Sorghum     10C   10G,1C                                                                              10G   10C   6C   2U,9G 3C,9G                                                                              2U,9G 3U                  Corn        10C   10G,7U                                                                              9G,5C 10C   9C   9C    9C   3U,9G 3U                  Soybean     10G,5C                                                                              7G,3X 9G,5X 10G,3H,3C                                                                           9C   9C    2C,5H                                                                              2H,8G 3C                  Wheat       9G,3C 0 2G  9G,1C 2C    2C,5G                                                                              0     1C,9G                                                                              3C                        Wild Oats   10G,3C                                                                              0     1G    9G,1C 4C   1C    0    3C,9G 9C                  Rice        10G,5C                                                                              10G,2C                                                                              10G,2C                                                                              9C    5C   6C,9G 4C,9G                                                                              4C,9G 4C                  Barnyardgrass                                                                             10C   9C    9C    10C   9C   9C    5C,9H                                                                              6C,9H 9C                  Crabgrass   9G,7C 0     0     9C    3C   3C,7G 1C   2C,9G 3C                  Morningglory                                                                              10G,4C                                                                              6G    8G,2C 10G,10P,3C                                                                          9C   4C,8H 2C,7H                                                                              4C,7H 9C                  Cocklebur   10C   8G    4G    9G,2C 10C  2C,9H 2G   4C,9G 9C                  Cassia      10G,4C                                                                              5G    6G    10G,4C                                                                              9C   3C,7G 1C   4C,9G 9C                  Nutsedge    9G,8C 0     0     10G,2C                                                                              6C   5G    4G   1C,6G 5C                  __________________________________________________________________________                Cmpd. 19                                                                            Cmpd. 20                                                                            Cmpd. 21                                                                            Cmpd. 22                                                                            Cmpd. 23                                                                           Cmpd. 24                             __________________________________________________________________________    Bush bean   6C,9G,6Y                                                                            3C,9G,6Y                                                                            9C    9C    9C   9C                                   Cotton      9C    4C,9H 6C,9G 5C,9G 5C,9G                                                                              9C                                   Sorghum     8U,9G 2C,9G 3C,9G 5C,9G 2C,9H                                                                              2C,9G                                Corn        5C,9G 1C,3G 2C,6G 2C,7H 4U,9H                                                                              2U,9H                                Soybean     4C,9G 3H    1C,6H 3C,8H 3H   1H                                   Wheat       5C,9G 0     0     1C    0    0                                    Wild Oats   9C    0     3C    0     0    0                                    Rice        6C,9G 1C,9G 2C,9G 3C,9G 2C,8G                                                                              2C,8H                                Barnyardgrass                                                                             10C   2C,5H 4C,9H 5C,9H 2C,4H                                                                              1C,2H                                Crabgrass   2C,8G 0     1C,3H 1C,5H 1C,2G                                                                              1C                                   Morningglory                                                                              5C,9G 3C,8G 6C,9G 4C,9G 5C,9G                                                                              4C,8H                                Cocklebur   5C,9G 2C,8H 3C,9G 9C    6C,9G                                                                              4C,9G                                Cassia      9C    2C    3C,9H 9C    4C,8H                                                                              4C,7H                                Nutsedge    9C    0     1C,6G 3C,9G 1C   0                                    __________________________________________________________________________    PRE-EMERGENCE                                                                             Cmpd. 1                                                                             Cmpd. 2                                                                             Cmpd. 3                                                                             Cmpd. 4                                                                             Cmpd. 5                                                                            Cmpd. 6                                                                             Cmpd. 7                                                                            Cmpd.                                                                               Cmpd.               __________________________________________________________________________                                                              9                   Sorghum     6C,9G 2C,9H 10E   5C,9G 5C,9H                                                                              2C,8G 7G   10E   10E                 Corn        5C,9G 3C    10E   2U,9G 2C,9G                                                                              2C,8G 3C,7G                                                                              9G    10E                 Soybean     9H    2H    8H    9H    9H   1C,4G 1C,2H                                                                              9G    9G                  Wheat       9H    3C,9G 9H    4C,9G 2C,9G                                                                              5G    2G   10E   10E                 Wild Oats   5C,9G 2C,7G 3C,9G 5C,9G 4C,9G                                                                              0     2C   9G    9G,2C               Rice        10E   9H    10E   10E   10E  4C,9H 3C,8H                                                                              10E   10E                 Barnyardgrass                                                                             2C,9H 2C,6G 3C,9H 6C,9H 5C,9H                                                                              4C,6H 3C,8H                                                                              9G    9G,3C               Crabgrass   2C,8G 1C    5C,9G 5C,9G 5C,9G                                                                              1C    1C   9G    9G,4C               Morningglory                                                                              9H    2C,5H 9G    5C,9G 9G   8H    8G   9G    9G,3C               Cocklebur   9H    6G    9H    9H    9H   8H    8H   7G    9G,10P              Cassia      9G    3C    2C,9G 2C,8G 9G,2C                                                                              9G,5C 9G   8G    8G,2C               Nutsedge    9G    0     10E   2C,8G 10E  5G    1C,3G                                                                              9G    9G                  __________________________________________________________________________                Cmpd. 10                                                                            Cmpd. 11                                                                            Cmpd. 12                                                                            Cmpd. 13                                                                            Cmpd. 14                                                                           Cmpd. 15                                                                            Cmpd. 16                                                                           Cmpd.                                                                               Cmpd.               __________________________________________________________________________                                                              18                  Sorghum     10E   9G    9G    10E   10E  5C,9H 6C,9H                                                                              9H    10E                 Corn        9G    9G    9G    9G    10E  2C,9G 9H   9H    10H                 Soybean     9G    4G    5G    9G    9H   2C,7H 1C,2H                                                                              2H,5G 9H                  Wheat       9G,2H 0     0     9G    8G   1C,3G 0    2C,8G 9H                  Wild Oats   8G,3C 0     0     8G    1C,9G                                                                              2C,5G 0    8G    5C,9H               Rice        10E   4G,2C 8G    10E   10E  4C,8G 3C,6G                                                                              10E   10E                 Barnyardgrass                                                                             9G,2C 9G    9G,2C 9G,3C 4C,9H                                                                              5C,9H 2C,5H                                                                              4C,9H 5C,9H               Crabgrass   9G,2C 5G    2G    9G    4C,8G                                                                              1C    0    3G    2C,8G               Morningglory                                                                              9G    5G    7G    9G    9G   2C,5H 2H   9H    9G                  Cocklebur   8G    7G    7G    7G    9H   9H    0    9H    9H                  Cassia      8G    8G    8G    8G    6C,9G                                                                              4C,8H 2C   9G    9G,3C               Nutsedge    10E   0     4G    9G    10E  2C    O    7G    2C,9G               __________________________________________________________________________                Cmpd. 19                                                                            Cmpd. 20                                                                            Cmpd. 21                                                                            Cmpd. 22                                                                            Cmpd. 23                                                                           Cmpd. 24                             __________________________________________________________________________    Sorghum     5C,9H 2C,7H 9H    9H    3C,9H                                                                              2C,9H                                Corn        5C,9G 1C    2C,8G 3C,8H 2C,9G                                                                              2C,9G                                Soybean     9H    1H    2H    2G    1H   2A                                   Wheat       2C,8H 2G    0     1C,2G 0    0                                    Wild Oats   2C,9G 2C,6G 2C,8G 2C,6G 2C,7G                                                                              1C,4G                                Rice        10E   3C,6G 2C,8H 5C,8H 5C,9H                                                                              2C,8H                                Barnyardgrass                                                                             3C,9H 2C,7H 9H,2C 4C,9H 1C,5H                                                                              3C,7H                                Crabgrass   2C,5G 1C    5G    1C,3G 1C   1C                                   Morningglory                                                                              9H    6H,2C 9H    9H    8H,2C                                                                              2C,7H                                Cocklebur   9H    2C,2H 9H    --    3C,8H                                                                              9H                                   Cassia      5C,9G 3C    3C,6H 2C,5H 5C   4C,6H                                Nutsedge    10E   0     6G    10E   0    0                                    __________________________________________________________________________

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grassy weeds. The other pan was planted withcotton, soybeans, purple nutsedge (Cyperus rotundus), and severalbroadleaf weeds. The following grassy and broadleaf weeds were planted:crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur(Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory(Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa),velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A12.5 cm diameter plastic pot was also filled with prepared soil andplanted with rice and wheat. Another 12.5 cm pot was planted withsugarbeets. The above four containers were treated pre-emergence withseveral test compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B.

                  TABLE B                                                         ______________________________________                                        PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                                       Compound 1                                                     Rate kg/ha       0.03        0.12                                             ______________________________________                                        Crabgrass        5G          7G,3H                                            Barnyardgrass    7G,3H       8G,8C                                            Sorghum          9G,8C       10E                                              Wild Oats        6G          6G,3C                                            Johnsongrass     7G,5H       8G,5H                                            Dallisgrass      5G,2H       7G,3H                                            Giant Foxtail    7G,5H       8G,5H                                            Ky. Bluegrass    4G          6G,3H                                            Cheatgrass       7G,3H       8G,9C                                            Sugarbeets       8G,8C       9G,9C                                            Corn             4G          7G,5H                                            Mustard          9G,9C       9G,9C                                            Cocklebur        5G          8G,3H                                            Pigweed          --          --                                               Nutsedge         5G          8G                                               Cotton           5G,5H       8G,5H                                            Morningglory     7G,5H       9G,5H                                            Cassia           7G          8G,5C                                            Teaweed          5G,3C       8G,8C                                            Velvetleaf       4G,5H       8G,6C                                            Jimsonweed       8G,8C       8G,9C                                            Soybean          5G,5H       9G,5H                                            Rice             8G,8E       10E                                              Wheat            3G          8G,8E                                            ______________________________________                                    

Test C

Twenty-five cm diameter plastic pots filled with Fallsington silt loamwere planted to soybeans, cotton, alfalfa, corn, rice, wheat, sorghum,velvetleaf, (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia(Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Daturastramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitariaspp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloacrusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua).Approximately 21/2 weeks after planting, the young plants and the soilaround them were sprayed overall with the test chemicals dissolved in anon-phytotoxic solvent. Fourteen days after treatment, all species werecompared to untreated controls and visually rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table C.

                  TABLE C                                                         ______________________________________                                        Over-the-Top Soil/Foliage Treatment                                                    Compound 1    Compound 2                                             Rate kg/ha 0.06      0.016     0.06   0.016                                   ______________________________________                                        Soybeans   10G,8C    10G,8C    8G,5C  5G,2C                                   Velvetleaf 10C       10C       8G,2C  7G,5C                                   Sesbania   10C       7G,2C     2G,3C  3C                                      Cassia     7G,2C     8G,3C     7G,2C  3G,3C                                   Cotton     10C       10C       8G,3C  4G,3C                                   Morningglory                                                                             6G,1C     5G,1C     8G,2C  3G                                      Alfalfa    7G,4C     7G,4C     7G,4C  1G,2C                                   Jimsonweed 2C        2C        0      5G                                      Cocklebur  8G,2C     5G,1C     5G,1C  0                                       Corn       8G,1C     7G,4C     1C     1G                                      Crabgrass  7G        6G        1G     4G                                      Rice       5G,1C     6G        5G,2C  4G                                      Nutsedge   4G        3G        0      1G                                      Barnyardgrass                                                                            7G,1C     7G        6G,1C  0                                       Wheat      5G        4G        4G     4G                                      Giant foxtail                                                                            9G        7G        0      0                                       Wild Oats  6G        6G        3G     2G                                      Sorghum    7G,1C     6G,1C     4G     4G,3C                                   Mustard    10C       9G,9C     9G,5C  6G,1C                                   Pigweed    --        --        --     --                                      Johnsongrass                                                                             --        --        --     --                                      Sunflower  10C       10C       8G,5C  --                                      Sugarbeets 10C       6G,1C     7G,1C  6G,1C                                   ______________________________________                                    

What is claimed is:
 1. A compound of the formula: ##STR103## wherein Qis O or S;A is ##STR104## R₁ is R₆ S(O)_(n) ; R₆ is C₁ -C₄ alkyl, C₃ -C₄alkenyl, cyclopentyl or cyclopropylmethyl; R₂ is H, Cl, Br or CH₃ ; R₃and R₄ are independently H or CH₃ ; n is 0, 1 or 2; and R₅ is ##STR105##wherein X is CH₃ or OCH₃ ; Y is H, Cl, CH₃, C₂ H₅, OCH₃, OC₂ H₅ or CH₂OCH₃ ; Y₁ is H, Cl, CH₃ or OCH₃ ; Y₂ is CH₃ or OCH₃ ; Z is CH;and theiragriculturally suitable salts; provided that: both R₃ and R₄ may notsimultaneously be CH₃, and further provided that R₁ and A are bonded toadjacent carbon atoms of the thiophene or furan ring.
 2. Compounds ofclaim 1 wherein Q is S.
 3. Compounds of claim 2 where R₂ is H. 4.Compounds of claim 3 where R₆ is C₁ -C₃ alkyl.
 5. Compounds of claim 4where n is
 2. 6. Compounds of claim 5 where R₅ is ##STR106## 7.Compounds of claim 6 where R₃ is H.
 8. Compounds of claim 7 with thestructure ##STR107##
 9. Compounds of claim 7 with the structure##STR108##
 10. Compounds of claim 7 with the structure ##STR109## 11.Compounds of claim 8 where X is CH₃ or OCH₃ ; and Y is CH₃, OCH₃, OC₂ H₅or CH₂ OCH₃.
 12. Compounds of claim 9 where X is CH₃ or OCH₃ ; and Y isCH₃, OCH₃, OC₂ H₅ or CH₂ OCH₃.
 13. Compounds of claim 10 where X is CH₃or OCH₃ ; and Y is CH₃, OCH₃, OC₂ H₅ or CH₂ OCH₃.
 14. Compounds of claim11 where R₄ is H.
 15. Compounds of claim 12 where R₄ is H.
 16. Compoundsof claim 13 where R₄ is H.
 17. Compounds of claim 1 where Q is O. 18.Compounds of claim 17 where R₂ is H.
 19. Compounds of claim 18 where R₆is C₁ -C₃ alkyl.
 20. Compounds of claim 19 where n is
 2. 21. Compoundsof claim 20 where R₅ is ##STR110##
 22. Compounds of claim 21 where R₃ isH.
 23. Compounds of claim 22 with the structure ##STR111##
 24. Compoundsof claim 22 with the structure ##STR112##
 25. Compounds of claim 22 withthe structure ##STR113##
 26. The compound of claim 1,N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide.27. The compound of claim 1,N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide.28. The compound of claim 1,N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide.29. The compound of claim 1,N-[(4,6-dimethoxypyrimidin-2-yl)(methyl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide.30. The compound of claim 1,N-[(4-methoxy-6-methylpyrimidin-2-yl)(methyl)aminocarbonyl]-2-(methylsulfonyl)-3-thiophenesulfonamide.31. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 1and at least one of the following: surfactant, solid or liquid diluent.32. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 2and at least one of the following: surfactant, solid or liquid diluent.33. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 3and at least one of the following: surfactant, solid or liquid diluent.34. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 4and at least one of the following: surfactant, solid or liquid diluent.35. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 5and at least one of the following: surfactant, solid or liquid diluent.36. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 6and at least one of the following: surfactant, solid or liquid diluent.37. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 7and at least one of the following: surfactant, solid or liquid diluent.38. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 8and at least one of the following: surfactant, solid or liquid diluent.39. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 9and at least one of the following: surfactant, solid or liquid diluent.40. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 10and at least one of the following: surfactant, solid or liquid diluent.41. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 1. 42. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 2. 43. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim3.
 44. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 4. 45. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 5. 46. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim6.
 47. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 7. 48. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 8. 49. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim9.
 50. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim 10.